


Five Futures for Toby Flenderson

by Kyra



Category: The Office (US)
Genre: 5 Things, Bittersweet Ending, Choose Your Own Ending, Costa Rica, Divorce, Endgame, Enemies, F/M, Fatherhood, Friendship, Future Fic, Gen, Happy Ending, KaPam, Last Time, Male Friendship, Parenthood, Retirement, Season/Series 03, Surfing, Unhappy Ending, Wish Fulfillment, Workplace, Workplace Relationship, fathers and daughters, frienemies
Language: English
Status: Completed
Published: 2006-11-30
Updated: 2006-11-30
Packaged: 2018-01-03 23:41:24
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,874
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1074423
Author URL: https://archiveofourown.org/users/Kyra/pseuds/Kyra
Summary: <blockquote class="userstuff">
              <p>The first thing he learns is that he's really terrible at surfing.</p>
            </blockquote>





	Five Futures for Toby Flenderson

**Author's Note:**

> Five alternate futures for Toby. Many pairings. Mucho thanks to agate for beta-ing!
> 
> Written November 2006 (omfg).

**1\. the right decision for me and my marriage**

Toby sleeps with his ex-wife again on New Year's Eve 2007. It's been four-and-a-half years since the last time they did this, and he feels half a step removed from everything: noticing how she touches him in the same places, how her hair is shorter, how his life feels heavier. It's dark, and the blinds cast shadows on the wall above the bed; one of the other apartments in the complex is having a party, and the music sounds like it's underwater, muffled and distant.

He's a little drunk but so is she. Earlier he'd seen her laugh for the first time in a long time, at him, at something Sasha was making him do as a human prop in an elaborate production of some Disney movie. Now Sasha's asleep in the next room, so they're quiet, so quiet. She bites down on his shoulder when she comes.

The last time they did this, he didn't know it would be the last time. He knew things were bad, but you never know where the line is going to fall.

Once upon a time he imagined this, how if he got one more chance he'd find exactly the right thing to say about them, about how good they were together, about how they could make it work. How nothing feels right when he doesn't wake up to her beside him, and doesn't she miss him, too? It seems far away, caring that much.

Now he sits with his elbows on his knees and watches her pull her shirt on. When she looks up from tying her shoes he notices with vague surprise the lines around her eyes, how the look she gives him is just about as lost and tired as he's felt for years and years now.

It's for the best, she'll say in a minute, and he'll kiss her temple and when he agrees he'll be surprised to realize he means it, more or less.

**2\. I didn't really think you could win desert island, but I think you just did**

Jim comes back sadder. Toby'd been the first to get the list of the personnel who'd be transferring, and he'd smiled a little to himself as he started processing it. He and Jim have always gotten along well, though they talked less after Pam started working there, and when Michael separated them so he could stick Toby in the back.

Before that, he and Jim used to play complex games of house rules Uno across their desks when Michael wasn't looking, and Jim would talk wistfully about stuff he used to do in college. After Toby moved, they e-mailed about whatever movies they'd seen over the weekend. "Delete this immediately" or "Highly confidential" was Jim's subject line whenever he admitted to liking something truly terrible. Twice he babysat Sasha while Toby went on mediocre dates, and when it was her mom's weekend, sometimes he'd go crash on Jim's couch for an evening and play videogames with his roommate.

But Jim comes back and he acts like knocking knuckles with Toby is something they've never done before, and the next week when Toby asks him in the breakroom if he's seen any good movies lately, he just shrugs and pops a baby carrot in his mouth and says "not really". Even Dwight almost never complains about him anymore, although he provides more than enough write-ups on Andy to keep Toby busy.

All winter Jim acts like there's a bubble around him, like if he pretends he's not really here, he won't be. "Ohmigod, Jim, this is like the most you've sold EVER," Kelly says from the other side of the partition every time he brings the sales totals by for her to update, and one time when Toby asks Ryan what's up after he wanders by looking particularly peeved, Ryan mutters something about Jim getting on his case about his numbers.

One of the new people, Karen, likes to sit on Jim's desk when Michael's not around and tell him weird websites to look up, and after a month Toby catches them kissing in the kitchen. Karen looks happy, but Jim won't meet his eye, and a month after that Toby's in the parking lot when he hears Karen say "what is _wrong_ with you?" and slam the door to Jim's car.

Jim stops taking lunch breaks after that, and Karen keeps to herself so much that Toby thinks he's going to have to ask if she's all right. It's Pam, though, who starts hanging out with her -- at lunch, at mandatory parties, during endless Michael sessions in the conference room. Toby's talking to Creed one day when Pam lets out a sharp bark of laughter at her computer screen, then covers her mouth, turning to look at Karen. Karen bites her pen and grins, and Toby pretends he doesn't see the look on Jim's face.

(It's Karen who talks Toby into greenlighting two-hour lunches for her and Pam twice a week, if they skip lunch two other days, and if they both come back with their faces flushed, laughing a little too much, it's probably the least egregious violation of Dunder Mifflin's alcohol policy in Toby's tenure.)

Toby doesn't realize it's February 13th until he's leaving for the day. He and Jim are the only two people left in the office, and Jim looks up as Toby's pulling on his coat.

"Oh, hey!" he says, and it sounds so much like the old Jim that Toby has a weird flash of deja vu. "Um, so, we're doing the whole Valentine's Day poker game thing again this year," he says. "Tomorrow night. At Mark's house. You remember Mark, right?"

"Yeah," says Toby dumbly. Mark always claimed Toby brought the best beer when they were having people over. "Why can't you be more like this guy, Halpert?" he'd say, knocking Jim on the shoulder. Toby realizes he hasn't said anything else and Jim is looking awkward.

"Look," Jim says, scratching the back of his head. "I know I've been kind of a dick lately. But, um, I've realized that's getting pretty lame. And, uh, it would be really cool if you could come. If you're not busy. We haven't hung out in like forever."

"Okay," says Toby. "Sure." He smiles, and Jim smiles back, looking relieved.

"Awesome," he says. "It should be fun. Hey, how's Sasha?"

Jim comes out of the building just as Toby's getting in his car, and lifts his hand. Toby waves back and starts thinking about what kind of beer to bring.

 

**3\. Costa Rica**

The first thing he learns is that he's really terrible at surfing. He's staying in a rundown motel by the beach, and every morning he walks a mile to the bigger resort area, where he's found a local guy who's giving him lessons for cheap. Eventually he's going to have to find somewhere more permanent to live; the severance package he got when Dunder Mifflin finally went under isn't going to last forever. (He has Jan to thank for the fact that he got a severance package from a bankrupt company at all. He hopes that whatever she's doing now, it's less miserable.)

Surfing is _hard_ ; every night he goes to bed hurting everywhere. Dull general aches, and sharper bruises from where his board smacked into him. His surf instructor rolls his eyes and paddles out beside him again, but when Toby comes back day after day and doesn't give up, he gets friendlier. The first time Toby rides a wave the entire way to shore without wiping out, he feels something in his chest release, like he's been wanting this so long he forgot what it was like to be happy.

After a while he finds a bungalow further inland that costs less per month than he paid in a week for his condo back home, and even longer after that his old surf instructor starts inviting him to the little local bar, where his friends make good-natured fun of Toby in Spanish he can almost understand. At night he can hear monkeys howling in the distance, and eventually he stops noticing the rice and beans in the gutters. He gets parasites once. His barber starts remembering his name. He realizes one day that he can't remember a single Dunder Mifflin phone number.

Once a week he walks out to the touristy areas and checks his e-mail -- he'd go without, if he could, but his ex-wife sends him pictures of Sasha, her first day of school, at her dance recital, as the flower girl when her mother remarries.

By the time she comes to visit him for summer vacation, she's so tall he almost doesn't recognize her in the airport. Her face has lost its baby roundness, and her hair is longer and more prone to tangles, but it turns out he remembers exactly how to comb it out after her bath. She's shy around him for the first day, and then he takes her swimming and she lights up all over.

When he first moved here, he called her every other day on a crackly international connection, and every time she asked him when he was coming home to Scranton, and every time it broke his heart. Now she snuggles against him as they sit out on the porch, a warm, sleepy weight.

"I like Costa Rica," she says, half asleep, and he kisses the top of her head. All the stars are coming out.

 

**4\. you take what you get**

Toby asks Pam out on January 3, because a New Year's resolution is a New Year's resolution. She doesn't get it at first.

"Oh, is that what Oscar was talking about earlier?" she asks, and he shakes his head, makes himself look up from his hands on the edge of her desk.

"No, I mean, like, just you and me, for dinner... or something."

"Oh," she says. " _Oh._ " She looks surprised, but at least she hasn't laughed in his face yet. "Um," she says, and then the phone rings and she smiles apologetically.

"What?" she says, and he follows her gaze to Michael on the phone in his office. "Why can't you ask him yourself?" She pauses, listening. "Fine," she says, then covers the mouthpiece. "Andy," she calls. "Michael wants to see you in his office."

"What?" Dwight says, standing up immediately. "Just Andy? Why?" Pam sighs and rolls her eyes at Toby.

"I don't know, Dwight, he just--"

"Is that him now?" Dwight says, coming toward her and the phone, just as Andy walks by smugly, and knocks into Dwight with his shoulder. Toby sneaks back to his desk during all the yelling, and tries to focus on work.

Pam comes by after lunch to turn him down, and he braces himself. At least Kelly isn't at her desk.

"Hey, um," she says, shifting from foot to foot. "About earlier..."

"It's okay," he says quickly. "You don't have to... don't worry about it." She blinks.

"No," she says. "I was, um, going to say that I'm free Saturday."

It's weird, at first-- he's not sure if he should pull out her chair for her, but she's sitting down before he gets to decide either way, and they make stilted small talk about the paintings in the restaurant. It's Angela, of all things, that breaks the ice.

"Oh my god, you never got invited to any of the cat parties?" Pam laughs. "That's outrageous!"

Toby shrugs, grinning, and looks down at his half-empty plate.

"No, but she _did_ complain to me that people weren't RSVPing in a timely manner." This is breaking about 14 rules of professional confidentiality. He doesn't care.

They get dessert, and he drives her home, and says "okay, well, um," when he pulls into her driveway. When she kisses him it's quick, and she's blushing when she pulls back, but he feels it all the way home.

She starts coming over his house in the evening sometimes, and they rent the movies he's appalled she's never seen, or the movies she's appalled he's never seen, or movies they've both seen twenty times. She's different outside of work -- happier, maybe. Less guarded. Sometimes he looks over at her sitting on his couch, feet on his lap, and feels strange. On the weekends, she has art school classes and he runs and watches Sasha, if it's his turn. Pam comes to one of his races and hugs him at the finish line even though he's all sweaty. He takes her to restaurants in Wilkes-Barre where she's never been and gives her daisies on Valentine's Day because she has a painting of them in her living room.

Every day he expects her to tell him this was all a mistake, and she never does.

"This is nice," she says instead, muzzily, after the second time they sleep together. "You know?" She's asleep a minute later, and he looks at the ceiling and listens to her breathe.

She's the first real relationship he's had since his divorce. He calls her his ex-wife's name exactly once, while he's washing the dishes at her place. It's okay, it's okay, it's okay, she says. She never talks about Roy at all, but sometimes Toby sees them talking in the parking lot.

They haven't told anyone at work, by mutual agreement; it's bad enough with Kelly all over Ryan, and Andy smarmily flirting with Angela, and Jim's hand on Karen's waist every time Toby turns around.

"They seem serious," Pam says watching, them across the conference room; Karen's leaning into Jim under the Kiss Me, I'm Irish banner, her hand on his chest, and he's smiling.

"What?" says Toby. "Yeah, I guess."

"Karen told me they might move in together when her lease is up," Pam says, but before he can say anything she looks away from them, back at him. "Hey, do you know what Sasha wants for her birthday?"

Pam leaves her earrings on his bedtable accidentally and he's giving them to her at her desk the next morning, when her gaze shifts over his shoulder, smile fading. When he turns around, it's Jim, looking at them both, and Toby can see him getting it.

"Hey," he says, and Pam looks momentarily stricken. Toby tries not to take it personally.

"Jim," she says, as he walks by, but he doesn't stop. Toby finds him later in the conference room, buried in paperwork.

"Hey," he says, "I just wanted to make sure, um--"

"No, don't worry about it," Jim says without looking up. "It's fine. We're cool."

At Easter, Pam hides plastic eggs all over the apartment for Sasha to find, and laughs when she starts jumping on the bed, mouth and hands sticky. Sometimes Toby catches her looking at him with a strange, surprised look on her face, like maybe she didn't expect any of this. He knows the feeling.

They run into Jim and Karen at Poor Richard's and end up spending an incredibly awkward evening sitting together. Toby's known about Jim's Pam thing for as long as he can remember, way before Jim started complaining to him about her wedding plans and the workplace. He's always figured that will be why Pam leaves him.

It's warm out for early May when they finally leave the bar. Tomorrow night is Michael's annual casino event; the thought already makes him tired. Pam is quiet beside him, and when he looks at her she smiles wearily and winds her fingers with his. They walk all the way to her car that way, and he can't tell what she's thinking at all.

 

**5\. the things you choose to be**

Michael Scott's retirement party is held at 4:45 on a Tuesday; Michael cries and everyone else stands around looking uncomfortable. Vintage Dunder Mifflin.

There's champagne that tastes more like fizzy vinegar, and Toby is thoughtfully swirling it around in his plastic cup, when Michael comes up beside him.

"Well," he says. "You must be pretty happy."

"Why?" says Toby, and Michael makes a face that could be either 'I loathe your being' or 'I'm trying not to cry'.

"Because you win," he says. "I'm leaving. The place is yours now."

"Michael," says Toby. "It's not really--"

"Don't you hurt these people," Michael says. "They are good people."

"... okay, Michael," says Toby.

"And don't you let them forget me, either," says Michael, voice thick.

"I won't," says Toby.

"Oh, why am I talking to you anyway?" Michael says.

After he leaves, the newest receptionist wanders up to Toby. They look younger and younger these days, which is strange because everyone else looks older: Phyllis, himself in the mirror, his kids. He has to drive Sasha back to college next week -- junior year already.

"So you guys must have worked together forever, huh?" Mindy says. Or is it Mandy? He's never been good with names.

"Yep," says Toby. "Just about." They watch Michael mournfully show a box of plaques to one of the sales guys.

"Are you going to miss him?" she says, and Toby shrugs before he realizes he knows the answer. He feels himself starting to smile.


End file.
